EA008191B1 - Сшитые блок-сополимеры стирола и способ их получения - Google Patents
Сшитые блок-сополимеры стирола и способ их получения Download PDFInfo
- Publication number
- EA008191B1 EA008191B1 EA200500161A EA200500161A EA008191B1 EA 008191 B1 EA008191 B1 EA 008191B1 EA 200500161 A EA200500161 A EA 200500161A EA 200500161 A EA200500161 A EA 200500161A EA 008191 B1 EA008191 B1 EA 008191B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- styrene
- polymer
- block copolymer
- bitumen
- living
- Prior art date
Links
- 229920006132 styrene block copolymer Polymers 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 54
- 239000010426 asphalt Substances 0.000 claims abstract description 44
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- -1 alkyl compound Chemical class 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 239000004568 cement Substances 0.000 claims abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 57
- 229920001400 block copolymer Polymers 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000001993 dienes Chemical group 0.000 claims description 14
- 239000003431 cross linking reagent Substances 0.000 claims description 12
- 150000005690 diesters Chemical class 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 239000011414 polymer cement Substances 0.000 claims description 10
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 3
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims 1
- 229920002857 polybutadiene Polymers 0.000 claims 1
- 229920001195 polyisoprene Polymers 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 3
- 230000004048 modification Effects 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract description 2
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 22
- 238000004132 cross linking Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000011269 tar Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- ABIAVOPWHAWUGT-UHFFFAOYSA-N zinc;2-methanidylpropane Chemical compound [Zn+2].CC(C)[CH2-].CC(C)[CH2-] ABIAVOPWHAWUGT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
- C08F297/044—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes using a coupling agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
- C08L53/025—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes modified
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Civil Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39513902P | 2002-07-11 | 2002-07-11 | |
| PCT/US2003/021814 WO2004007581A1 (en) | 2002-07-11 | 2003-07-11 | Coupled styrenic block copolymers and process for preparing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200500161A1 EA200500161A1 (ru) | 2005-08-25 |
| EA008191B1 true EA008191B1 (ru) | 2007-04-27 |
Family
ID=30115821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200500161A EA008191B1 (ru) | 2002-07-11 | 2003-07-11 | Сшитые блок-сополимеры стирола и способ их получения |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7009000B2 (ko) |
| EP (1) | EP1532185B1 (ko) |
| JP (1) | JP4368303B2 (ko) |
| KR (1) | KR100626442B1 (ko) |
| CN (1) | CN1302036C (ko) |
| AT (1) | ATE397632T1 (ko) |
| AU (1) | AU2003249169A1 (ko) |
| BR (1) | BR0312603B1 (ko) |
| DE (1) | DE60321467D1 (ko) |
| EA (1) | EA008191B1 (ko) |
| ES (1) | ES2307979T3 (ko) |
| WO (1) | WO2004007581A1 (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9328235B2 (en) | 2008-07-21 | 2016-05-03 | Lg Chem, Ltd. | Asphalt modifier composition and asphalt composition comprising the same |
| RU2703175C2 (ru) * | 2010-05-31 | 2019-10-15 | Бриджстоун Корпорейшн | Содержащий гидроксильные группы метилстирол и полимеры на его основе |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7125940B2 (en) | 2002-12-31 | 2006-10-24 | Kraton Polymers U.S. Llc | Conjugated diene polymers and copolymer blocks and process for preparing same |
| US8151281B2 (en) | 2004-01-09 | 2012-04-03 | International Business Machines Corporation | Method and system of mapping at least one web service to at least one OSGi service |
| US7465768B2 (en) * | 2004-06-18 | 2008-12-16 | Bridgestone Corporation | Method to reduce coupling during termination with functional end-groups |
| US7449518B2 (en) * | 2006-03-24 | 2008-11-11 | Kraton Polymers U.S. Llc | High temperature block copolymers and process for making same |
| KR100923535B1 (ko) * | 2007-11-21 | 2009-10-27 | 금호석유화학 주식회사 | 테이퍼드된 블록 공중합체를 함유한 개질 아스팔트 조성물 |
| US8883927B2 (en) * | 2007-11-28 | 2014-11-11 | Dynasol Elastómeros, S.A. De C.V. | Radial multi-block copolymers |
| CN101903455B (zh) | 2007-12-21 | 2013-01-16 | 科腾聚合物美国有限责任公司 | 软质弹性体膜 |
| US20100316820A1 (en) * | 2009-06-16 | 2010-12-16 | Rainer Kolb | Composite Materials Comprising Propylene-Based Polymer Blend Coatings |
| WO2011053406A1 (en) * | 2009-10-29 | 2011-05-05 | Exxonmobil Chemical Patents Inc. | Pressure-sensitive hot melt adhesive compositions |
| US9023950B2 (en) | 2010-04-21 | 2015-05-05 | Nippon Soda Co., Ltd. | Star polymer and method of producing same |
| KR101411159B1 (ko) * | 2010-08-03 | 2014-06-23 | 주식회사 엘지화학 | 아스팔트의 열 안정성 개선을 위한 삼중 가지형 비닐 방향족 탄화수소-공액디엔 블록 공중합체 조성물, 이의 제조방법, 및 이를 포함하는 아스팔트 조성물 |
| WO2015054457A1 (en) * | 2013-10-11 | 2015-04-16 | Kraton Polymers U.S. Llc | An olefinically unsaturated radial styrenic block copolymer and an improved vulcanizer-free latex |
| US10472514B2 (en) * | 2014-01-23 | 2019-11-12 | Asahi Kasei Kabushiki Kaisha | Block copolymer composition and adhesive composition |
| KR101688504B1 (ko) * | 2014-07-15 | 2016-12-22 | 금호석유화학 주식회사 | 개질 아스팔트용 첨가제 조성물, 이를 포함하는 개질 아스팔트 조성물, 및 그 제조 방법 |
| US9428628B2 (en) | 2014-08-20 | 2016-08-30 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
| US10385156B2 (en) | 2016-06-30 | 2019-08-20 | Kraton Polymers U.S. Llc | Performance high vinyl block copolymer compositions and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5272214A (en) * | 1986-12-01 | 1993-12-21 | Enichem Elastomeri S.P.A. | Radial and branched block copolymers, compositions which contain them, their preparation and their use in bituminous compositions |
| US5552493A (en) * | 1995-05-30 | 1996-09-03 | Shell Oil Company | Method for producing asymmetric radial polymers |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3631006A (en) | 1965-09-01 | 1971-12-28 | Cities Service Co | Process for the anionic polymerization of unsaturated hydrocarbon monomers |
| US4518753A (en) | 1982-04-26 | 1985-05-21 | National Research Development Corporation | Anionic polymerization of conjugated dienes in the presence of hindered triaryl boron or aluminum derivatives |
| US4530984A (en) | 1982-07-01 | 1985-07-23 | The Firestone Tire & Rubber Company | Process for production of polymers having increased 1,2-microstructure |
| US4476240A (en) | 1982-07-01 | 1984-10-09 | The Firestone Tire & Rubber Company | Catalyst system containing an anionic initiator based on lithium and phosphine oxide modifier |
| US4473661A (en) | 1982-07-01 | 1984-09-25 | The Firestone Tire & Rubber Company | Polymerization catalyst system containing organolithium, dialkyl magnesium and/or trialkyl aluminum, and a phosphine oxide |
| US4429091A (en) | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators |
| US4429090A (en) | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Catalyst containing oligomeric oxolanyl alkane modifiers and process for the production of polymers having increased 1,2-microstructure |
| US4480075A (en) | 1983-06-24 | 1984-10-30 | Shell Oil Company | Block copolymers of Ziegler-Natta polymerized and anionically polymerized monomers |
| US4591624A (en) | 1984-07-02 | 1986-05-27 | The Firestone Tire & Rubber Company | Catalyst system and process for polymerizing conjugated dienes |
| US4520123A (en) | 1984-07-02 | 1985-05-28 | The Firestone Tire & Rubber Company | Catalyst system and process for polymerizing conjugated dienes |
| US5202499A (en) | 1988-05-31 | 1993-04-13 | Gencorp Inc. | Liquid telechelic polymers having high 1,4-diene structure |
| US5063190A (en) | 1988-05-31 | 1991-11-05 | Gencorp Inc. | Anionic initiator system for polymerizing monomers |
| US5216181A (en) | 1988-05-31 | 1993-06-01 | Gencorp Inc. | Liquid telechelic polymers having high 1,4-diene structure |
| US4889900A (en) | 1989-06-12 | 1989-12-26 | Shell Oil Company | Preparation of alkyl methacrylate monomers for anionic polymerization |
| GB9002804D0 (en) | 1990-02-08 | 1990-04-04 | Secr Defence | Anionic polymerisation |
| US5397851A (en) | 1993-11-09 | 1995-03-14 | Polysar Rubber Corporation | Process for cis-1,4-polybutadiene production with reduced gel formation |
| US5376745A (en) | 1993-12-01 | 1994-12-27 | Shell Oil Company | Low viscosity terminally functionalized isoprene polymers |
| FR2714384B1 (fr) * | 1993-12-29 | 1996-02-02 | Atochem Elf Sa | Copolymère bloc étoile d'un monomère vinylaromatique et d'un diène conjugué, son procédé d'obtention, et les compositions comprenant ledit copolymère et du polystyrène cristal. |
| US5416168A (en) | 1994-03-31 | 1995-05-16 | Shell Oil Company | Protected functional initiators for making terminally functionalized polymers |
| US5420203A (en) * | 1994-05-17 | 1995-05-30 | Shell Oil Company | Process for producing high diblock content block copolymer compositions |
| US5412045A (en) | 1994-09-16 | 1995-05-02 | Polysar Rubber Corporation | Preparation of high cis-1,4-polybutadiene with reduced gel |
| US5610227A (en) | 1995-06-07 | 1997-03-11 | Bridgestone/Firestone, Inc. | Lithium amino magnesiate polymerization initiators and elastomers having reduced hysteresis |
| US6429273B1 (en) | 1996-03-14 | 2002-08-06 | Asahi Kasei Kabushiki Kaisha | Process for the preparation of vinylic polymers, polymerization initiator for vinylic monomers, and styrene resin composition |
| KR100487452B1 (ko) | 1996-08-19 | 2005-05-09 | 바스프 악티엔게젤샤프트 | 음이온 중합 방법 |
| WO1998007766A1 (de) | 1996-08-19 | 1998-02-26 | Basf Aktiengesellschaft | Verfahren zur herstellung von dienpolymerisatlösungen in vinylaromatischen monomeren |
| US5665827A (en) | 1996-11-07 | 1997-09-09 | Bridgestone Corporation | Synthesis of multiblock polymers using group IIA and IIB metal cyclic organometallic initiators |
| US5700888A (en) | 1996-11-07 | 1997-12-23 | Bridgestone Corporation | Synthesis of macrocyclic polymers having low hysteresis compounded properties |
| US5677399A (en) | 1996-11-07 | 1997-10-14 | Bridgestone Corporation | Synthesis of macrocyclic polymers with group IIA and IIB metal cyclic organometallic initiators |
| DE19648565A1 (de) | 1996-11-23 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung von Polyalkyl(meth)acrylaten |
| US6462143B1 (en) | 1998-02-03 | 2002-10-08 | Kraton Polymers Us Llc | Gel-free process for making functionalized anionically polymerized polymers |
| ES2211047T3 (es) * | 1998-02-07 | 2004-07-01 | Basf Aktiengesellschaft | Procedimiento para la obtencion de masas de moldeo termoplasticas, modificadas a la resiliencia. |
| US6242537B1 (en) | 1998-03-30 | 2001-06-05 | Shell Oil Company | Gel-free process for making hydrogenated functionalized anionically polymerized polymers |
| TW442498B (en) | 1998-05-18 | 2001-06-23 | Shell Internattonale Res Mij B | Process for making anionic polymeric di-and polyfunctional polymers using protected functional initiators, and functionalised polymer producted thereby |
| US6242538B1 (en) | 1998-06-04 | 2001-06-05 | Shell Oil Company | Process for making hydrogenated gel-free functionalized anionically polymerized polymers |
| US6455651B1 (en) | 1999-04-23 | 2002-09-24 | Kraton Polymers U.S. Llc | Uniform initiation of anionic polymerization using organo-substituted alkali metal initiators |
| US6391981B1 (en) | 1999-04-23 | 2002-05-21 | Kraton Polymers Us Llc | Increased throughput in the manufacture of anionic polymers by reduction in polymer cement viscosity through the addition of metal alkyls |
| US20030114611A1 (en) | 2001-10-24 | 2003-06-19 | Fmc Corporation | Functionalized alkyllithium formulations with improved thermal stability and processes for making the same |
| US20030114592A1 (en) | 2001-10-24 | 2003-06-19 | Fmc Corporation | Processes for improving stability of living polymer chain ends |
-
2003
- 2003-07-11 JP JP2004521737A patent/JP4368303B2/ja not_active Expired - Fee Related
- 2003-07-11 AU AU2003249169A patent/AU2003249169A1/en not_active Abandoned
- 2003-07-11 AT AT03764565T patent/ATE397632T1/de not_active IP Right Cessation
- 2003-07-11 CN CNB038197987A patent/CN1302036C/zh not_active Expired - Fee Related
- 2003-07-11 KR KR1020057000555A patent/KR100626442B1/ko active IP Right Grant
- 2003-07-11 WO PCT/US2003/021814 patent/WO2004007581A1/en active Application Filing
- 2003-07-11 EA EA200500161A patent/EA008191B1/ru not_active IP Right Cessation
- 2003-07-11 BR BRPI0312603-0A patent/BR0312603B1/pt not_active IP Right Cessation
- 2003-07-11 DE DE60321467T patent/DE60321467D1/de not_active Expired - Lifetime
- 2003-07-11 US US10/618,394 patent/US7009000B2/en not_active Expired - Lifetime
- 2003-07-11 EP EP03764565A patent/EP1532185B1/en not_active Expired - Lifetime
- 2003-07-11 ES ES03764565T patent/ES2307979T3/es not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5272214A (en) * | 1986-12-01 | 1993-12-21 | Enichem Elastomeri S.P.A. | Radial and branched block copolymers, compositions which contain them, their preparation and their use in bituminous compositions |
| US5552493A (en) * | 1995-05-30 | 1996-09-03 | Shell Oil Company | Method for producing asymmetric radial polymers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9328235B2 (en) | 2008-07-21 | 2016-05-03 | Lg Chem, Ltd. | Asphalt modifier composition and asphalt composition comprising the same |
| RU2703175C2 (ru) * | 2010-05-31 | 2019-10-15 | Бриджстоун Корпорейшн | Содержащий гидроксильные группы метилстирол и полимеры на его основе |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0312603B1 (pt) | 2012-12-11 |
| CN1302036C (zh) | 2007-02-28 |
| EA200500161A1 (ru) | 2005-08-25 |
| DE60321467D1 (de) | 2008-07-17 |
| BR0312603A (pt) | 2005-05-31 |
| JP4368303B2 (ja) | 2009-11-18 |
| WO2004007581A1 (en) | 2004-01-22 |
| JP2005533151A (ja) | 2005-11-04 |
| CN1675272A (zh) | 2005-09-28 |
| KR20050021458A (ko) | 2005-03-07 |
| AU2003249169A1 (en) | 2004-02-02 |
| US20040054090A1 (en) | 2004-03-18 |
| ES2307979T3 (es) | 2008-12-01 |
| ATE397632T1 (de) | 2008-06-15 |
| KR100626442B1 (ko) | 2006-09-20 |
| US7009000B2 (en) | 2006-03-07 |
| EP1532185A1 (en) | 2005-05-25 |
| EP1532185B1 (en) | 2008-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA008191B1 (ru) | Сшитые блок-сополимеры стирола и способ их получения | |
| RU2458091C2 (ru) | Композиция битумного вяжущего и способ ее получения | |
| KR100470395B1 (ko) | 역청조성물 | |
| CN113278296B (zh) | 逆向递变热塑性弹性体 | |
| CN104204014A (zh) | 经由植物油的原子转移自由基聚合的热塑性弹性体 | |
| US10442929B2 (en) | Asphalt modifier and asphalt composition comprising the same | |
| HU209708B (en) | Process for preparing bituminous compositions | |
| JP2000510898A (ja) | ビチューメン組成物、およびその製造方法 | |
| EP0728814B1 (en) | Bituminous composition | |
| US20210054209A1 (en) | Asphalt Modifier And Asphalt Composition Comprising Same | |
| RU2598084C2 (ru) | Способ получения привитых полимеров без использования инициатора или растворителя и битум-полимерные композиции, включающие указанные привитые полимеры | |
| JP4440931B2 (ja) | カップリングしたブロックコポリマー組成物の製造方法及び得られた組成物 | |
| USH1484H (en) | Method for obtaining polymer/bitumen blends with improved stability and polymer efficiency | |
| JPH07188360A (ja) | 不斉ラジアルポリマーの製造方法 | |
| CN110128606B (zh) | 嵌段共聚物和嵌段共聚物组合物和硫化橡胶及其应用和嵌段共聚物的制备方法 | |
| EP0423571B1 (de) | Verzweigte Copolymerisate | |
| JP2003519706A (ja) | Ｓ−ｂ−ｓ組成物 | |
| CN112745467B (zh) | 丁苯嵌段共聚物及其制备方法和应用以及改性沥青及其制备方法 | |
| KR102241925B1 (ko) | 블록 공중합체 조성물, 이의 제조방법 및 이를 포함하는 아스팔트 조성물 | |
| RU2821518C1 (ru) | Блок-сополимер, способ его получения и содержащая его асфальтовая композиция | |
| KR20210032811A (ko) | 블록 공중합체 조성물, 이의 제조방법 및 이를 포함하는 아스팔트 조성물 | |
| EP1174449A1 (en) | Monoalkenyl aromatic hydrocarbon-1, 3-conjugated diene block copolymers and waterproofing membranes comprising said copolymers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): RU |